EP3514187B1 - Composition de polythiol pour une lentille optique en plastique - Google Patents

Composition de polythiol pour une lentille optique en plastique Download PDF

Info

Publication number
EP3514187B1
EP3514187B1 EP19152675.5A EP19152675A EP3514187B1 EP 3514187 B1 EP3514187 B1 EP 3514187B1 EP 19152675 A EP19152675 A EP 19152675A EP 3514187 B1 EP3514187 B1 EP 3514187B1
Authority
EP
European Patent Office
Prior art keywords
polythiol
compound
composition
weight
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP19152675.5A
Other languages
German (de)
English (en)
Other versions
EP3514187A1 (fr
Inventor
Jongmin SHIM
Jung Hwan MYUNG
Seung Mo Hong
Hyuk Hee Han
Junghwan Shin
Hyeon Myeong Seo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SKC Co Ltd
Original Assignee
SKC Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by SKC Co Ltd filed Critical SKC Co Ltd
Publication of EP3514187A1 publication Critical patent/EP3514187A1/fr
Application granted granted Critical
Publication of EP3514187B1 publication Critical patent/EP3514187B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
    • C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/248—Catalysts containing metal compounds of tin inorganic compounds of tin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone

Definitions

  • Patent document 1 Japanese Laid-open Patent Publication No. Hei 7-252207
  • the invention provides a polythiol composition, which comprises a first polythiol compound having at least four mercapto groups only as a hydrogen-bondable functional group; and a second polythiol compound having at least two mercapto groups as a hydrogen-bondable functional group and at least one hydrogen-bondable functional group other than a mercapto group, wherein the first polythiol compound is a compound represented by the following Formula 1, 2, or 3; the second polythiol compound is a compound represented by the following Formula 4 or 5: and the hydrogen-bondable functional group other than a mercapto group in the second polythiol compound is a hydroxyl group, an amine group, an amide group, or a carboxyl group.
  • the first polythiol compound has 4 mercapto groups only as a hydrogen-bondable functional group; and the second polythiol compound has 2 or 3 mercapto groups as a hydrogen-bondable functional group and 1 or 2 hydrogen-bondable functional groups other than a mercapto group.
  • 2-mercaptoethanol may be reacted with a compound of Formula 6 in the presence of a base as a reaction catalyst to prepare a diol compound of Formula 7.
  • a base as a reaction catalyst
  • the reaction may be carried out at a temperature of -5 to 15°C, 0 to 12°C, or 5 to 10°C, for 2 to 10 hours, 2 to 8 hours, or 2 to 5 hours.
  • the amount of 2-mercaptoethanol may be 0.5 mole to 3 moles, particularly 0.7 mole to 2 moles, more particularly 0.9 mole to 1.1 moles, per 1 mole of the compound of Formula 6.
  • the base may be used in a catalytic amount.
  • the polyisocyanate compound is not particularly limited as long as it is a compound having at least two isocyanate groups in the molecule.
  • benzophenone-based, benzotriazole-based, salicylate-based, cyanoacrylate-based, oxanilide-based may be used.
  • the polythiol composition thus obtained contained 62% by weight of the polythiol compound (a second polythiol compound) represented by Formula 5, 17% by weight of the polythiol compound represented by Formula 4 (a second polythiol compound), 20% by weight of the polythiol compounds (a first polythiol compound) represented by Formulae 1 to 3, and 1% by weight of oligomeric compounds other than the Formulae 1 to 5.
  • the polymerizable compositions of Examples 1 to 3 and Comparative Examples 1 and 2 were each degassed and filtered.
  • the initial viscosity (A, cps) and the viscosity (Y, cps) after 5 hours were measured at 10°C using a non-contact viscometer (EMS-1000, Kyoto Electronics Manufacturing Co., Ltd.).
  • the change (D) in the viscosity was calculated with Equation 1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Eyeglasses (AREA)

Claims (6)

  1. Composition de polythiol, qui comprend un premier composé de polythiol présentant au moins quatre groupes mercapto uniquement comme groupe fonctionnel pouvant être lié à de l'hydrogène ; et
    un second composé de polythiol présentant au moins deux groupes mercapto comme groupe fonctionnel pouvant être lié à de l'hydrogène et au moins un groupe fonctionnel pouvant être lié à de l'hydrogène autre qu'un groupe mercapto,
    dans lequel le premier composé de polythiol est un composé représenté par les formules 1, 2 ou 3 suivantes ;
    le second composé de polythiol est un composé représenté par la formule 4 ou 5 suivante :
    Figure imgb0031
    Figure imgb0032
    Figure imgb0033
    Figure imgb0034
    Figure imgb0035
    Figure imgb0036
     et le groupe fonctionnel pouvant être lié à de l'hydrogène autre qu'un groupe mercapto dans le second composé de polythiol est un groupe hydroxyle, un groupe amine, un groupe amide, ou un groupe carboxyle.
  2. Composition de polythiol selon la revendication 1, qui comprend le premier composé de polythiol selon une quantité de 55 à 99,5 % en poids et le second composé de polythiol selon une quantité de 0,5 à 45 % en poids, sur la base du poids total de la composition de polythiol.
  3. Composition de polythiol selon la revendication 2, qui comprend le second composé de polythiol selon une quantité de 0,5 à 12 % en poids sur la base du poids total de la composition de polythiol.
  4. Composition polymérisable, qui comprend la composition de polythiol selon l'une quelconque des revendications 1 à 3 et un composé de polyisocyanate.
  5. Composition polymérisable selon la revendication 4, dans laquelle le composé de polyisocyanate est choisi dans le groupe consistant en du I,3-bis(isocyanatométhyl)cyclohexane, de l'hexaméthylène diisocyanate, du diisocyane isophorone, du diisocyanate de m-xylène, du diisocyanate de toluène, et un mélange de ceux-ci.
  6. Lentille optique, qui comprend une résine à base de polythiouréthane formée par le durcissement d'une composition polymérisable selon la revendication 4 ou la revendication 5.
EP19152675.5A 2018-01-19 2019-01-18 Composition de polythiol pour une lentille optique en plastique Active EP3514187B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020180007050A KR101894921B1 (ko) 2018-01-19 2018-01-19 플라스틱 광학 렌즈용 폴리티올 조성물

Publications (2)

Publication Number Publication Date
EP3514187A1 EP3514187A1 (fr) 2019-07-24
EP3514187B1 true EP3514187B1 (fr) 2020-07-29

Family

ID=63598262

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19152675.5A Active EP3514187B1 (fr) 2018-01-19 2019-01-18 Composition de polythiol pour une lentille optique en plastique

Country Status (6)

Country Link
US (1) US10435512B2 (fr)
EP (1) EP3514187B1 (fr)
JP (1) JP6700444B2 (fr)
KR (1) KR101894921B1 (fr)
CN (1) CN109627419B (fr)
TW (1) TWI675821B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101935031B1 (ko) * 2017-12-28 2019-01-03 에스케이씨 주식회사 플라스틱 광학 렌즈용 폴리티올 조성물
KR102564990B1 (ko) * 2020-12-01 2023-08-07 에스케이씨 주식회사 폴리티올 조성물 및 이를 포함하는 중합성 조성물
GB2615966A (en) * 2020-11-27 2023-08-23 Skc Co Ltd Polythiol composition, optical composition, and optical product
CN114605605B (zh) * 2022-03-08 2023-03-24 益丰新材料股份有限公司 一种含有多硫醇组合物的光学材料组合物

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68918356T2 (de) * 1988-07-14 1995-05-11 Mitsui Toatsu Chemicals Linse, ein Kunstharz mit hohem Brechungsindex enthaltend und Verfahren zur Herstellung der Linse.
FR2649711B1 (fr) * 1989-07-13 1993-01-22 Essilor Int Compositions de polymeres a base de polythiourethanes pour la fabrication de verres organiques
JPH0768326B2 (ja) * 1989-10-09 1995-07-26 三井東圧化学株式会社 ウレタン系レンズ用樹脂の製造方法
KR920007246B1 (ko) 1990-11-10 1992-08-28 현대자동차 주식회사 직접분사식 디이젤기관의 연소실
JP2695599B2 (ja) * 1993-09-29 1997-12-24 ホーヤ株式会社 ポリウレタンレンズの製造方法
US5608115A (en) * 1994-01-26 1997-03-04 Mitsui Toatsu Chemicals, Inc. Polythiol useful for preparing sulfur-containing urethane-based resin and process for producing the same
JPH09194558A (ja) 1996-01-23 1997-07-29 Mitsui Toatsu Chem Inc 含硫ウレタン系プラスチックレンズ
US5942158A (en) * 1998-03-09 1999-08-24 Ppg Industries Ohio, Inc. One-component optical resin composition
JP3974404B2 (ja) * 2002-01-15 2007-09-12 三井化学株式会社 ポリチオール、その製造方法、これを含有する重合性組成物、並びに樹脂及びレンズ
KR100973858B1 (ko) * 2005-04-11 2010-08-03 미쓰이 가가쿠 가부시키가이샤 폴리티오우레탄계 중합성 조성물 및 그것을 이용한 광학용수지의 제조 방법
JP5358182B2 (ja) * 2006-04-19 2013-12-04 三井化学株式会社 光学材料用（ポリ）チオール化合物の製造方法およびそれを含む重合性組成物
EP2559721B1 (fr) * 2006-05-05 2015-01-07 PPG Industries Ohio, Inc. Compositions et articles préparés à partir de polythiols oligomères à fonctionnalité thioéther
KR101400358B1 (ko) * 2012-05-23 2014-05-27 주식회사 케이오씨솔루션 신규한 폴리티올 화합물의 제조방법 및 이를 포함하는 광학재료용 중합성 조성물
JP5373226B1 (ja) 2012-08-14 2013-12-18 三井化学株式会社 ポリチオール組成物、光学材料用重合性組成物およびその用途
TW201506083A (zh) * 2013-06-18 2015-02-16 Mitsubishi Gas Chemical Co 光學材料用組成物
WO2015190809A1 (fr) * 2014-06-09 2015-12-17 주식회사 케이오씨솔루션 Nouveau composé de thiol et composition polymérisable le contenant
JP6438976B2 (ja) * 2015-02-02 2018-12-19 三井化学株式会社 光学材料用重合性組成物、光学材料およびその用途
EP3255017A4 (fr) * 2015-02-05 2018-10-10 Sekisui Chemical Co., Ltd. Couche intermédiaire pour verre feuilleté et verre feuilleté
KR102512167B1 (ko) * 2015-03-10 2023-03-21 가부시끼가이샤 도꾸야마 포토크로믹 경화체의 제조 방법
WO2016208707A1 (fr) * 2015-06-24 2016-12-29 三井化学株式会社 Procédé de fabrication d'un ester d'acide mercaptocarboxylique de pentaérythritol, composition polymérisable, résine, matériau optique, et lentille
KR101831892B1 (ko) * 2016-06-30 2018-02-26 에스케이씨 주식회사 폴리티오우레탄계 광학 재료용 중합성 조성물
JP6929930B2 (ja) * 2016-07-14 2021-09-01 エスケーシー カンパニー，リミテッド 光学材料のための芳香族ポリチオール化合物
JP6632493B2 (ja) * 2016-08-05 2020-01-22 ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ ポリチオール化合物の製造方法、硬化性組成物の製造方法、および硬化物の製造方法
JP6633990B2 (ja) * 2016-08-08 2020-01-22 ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ ポリチオール化合物の製造方法、硬化性組成物の製造方法、および硬化物の製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
JP2019128596A (ja) 2019-08-01
EP3514187A1 (fr) 2019-07-24
KR101894921B1 (ko) 2018-09-04
CN109627419A (zh) 2019-04-16
JP6700444B2 (ja) 2020-05-27
CN109627419B (zh) 2020-04-14
TWI675821B (zh) 2019-11-01
US20190225755A1 (en) 2019-07-25
TW201932449A (zh) 2019-08-16
US10435512B2 (en) 2019-10-08

Similar Documents

Publication Publication Date Title
EP3514187B1 (fr) Composition de polythiol pour une lentille optique en plastique
EP2853527B1 (fr) Nouveau procédé pour la préparation de composé de polythiol et composition polymère pour matériau optique comprenant ledit composé
KR101807584B1 (ko) 폴리티올화합물의 제조방법과 이를 이용한 우레탄계 광학재료용 수지 조성물
EP3486272B1 (fr) Composé polythiol aromatique pour matériau optique
KR101919258B1 (ko) 중합성 조성물, 투명 수지, 광학 재료, 플라스틱 렌즈 및 투명 수지의 제조 방법
TW201811741A (zh) 使用於光學材料製造的多元硫醇組成物及其製備方法
EP3505335B1 (fr) Composition de polythiol pour une lentille optique en plastique
KR20180089363A (ko) 광학 재료용 폴리티올 조성물 및 이의 제조방법
US10723697B2 (en) Preparation method of polythiol for optical lenses by using metal sulfide
KR101922168B1 (ko) 플라스틱 렌즈용 중합성 조성물
JP6957445B2 (ja) 光学材料用重合性組成物
EP3357948A1 (fr) Composition de polythiol pour lentille en plastique
EP3474046B1 (fr) Composition polymérisable pour lentille en plastique et procédé de préparation de lentille en plastique l'utilisant
KR101813258B1 (ko) 광학 재료용 실록산 티올 올리고머
KR20210121873A (ko) 티오우레탄계 광학재료용 수지 조성물과 티오우레탄계 광학재료용 수지의 제조방법
JP2866846B2 (ja) チオカルバミン酸ｓ−アルキルエステル系レンズ用樹脂の製造方法
US11578038B2 (en) Method for preparing polythiol composition
KR101883814B1 (ko) 광학 재료용 방향족 폴리티올 화합물
JP2018058922A (ja) 光学材料の製造方法
KR20080059322A (ko) 펜타에리스리톨메르캅토카본산에스테르의 제조방법, 그것에 의해 얻어진 펜타에리스리톨메르캅토카본산에스테르, 및 그 용도

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN PUBLISHED

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20200122

RBV Designated contracting states (corrected)

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

RIC1 Information provided on ipc code assigned before grant

Ipc: C08K 5/37 20060101ALI20200318BHEP

Ipc: C08K 5/521 20060101ALI20200318BHEP

Ipc: G02B 1/04 20060101ALI20200318BHEP

Ipc: C08G 18/76 20060101ALI20200318BHEP

Ipc: C08G 18/38 20060101AFI20200318BHEP

Ipc: C08K 5/00 20060101ALI20200318BHEP

INTG Intention to grant announced

Effective date: 20200330

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 1295708

Country of ref document: AT

Kind code of ref document: T

Effective date: 20200815

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602019000326

Country of ref document: DE

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

REG Reference to a national code

Ref country code: NL

Ref legal event code: MP

Effective date: 20200729

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 1295708

Country of ref document: AT

Kind code of ref document: T

Effective date: 20200729

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20201030

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20201029

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20201029

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20201130

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20201129

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602019000326

Country of ref document: DE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

26N No opposition filed

Effective date: 20210430

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20210118

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20210131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20210131

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20220131

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20220131

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20221220

Year of fee payment: 5

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20221221

Year of fee payment: 5

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230621

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO

Effective date: 20190118

REG Reference to a national code

Ref country code: DE

Ref legal event code: R081

Ref document number: 602019000326

Country of ref document: DE

Owner name: SK PUCORE CO., LTD., KR

Free format text: FORMER OWNER: SKC CO., LTD., SUWON-SI, GYEONGGI-DO, KR

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

Free format text: REGISTERED BETWEEN 20240201 AND 20240207

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IE

Payment date: 20240105

Year of fee payment: 6

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200729

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20240105

Year of fee payment: 6

Ref country code: GB

Payment date: 20240105

Year of fee payment: 6